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Compound Detail

CHEMBL571

KETOPROFEN
💊 Approved Drug
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💊 Approved Drug
CC(C(=O)O)c1cccc(C(=O)c2ccccc2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL571
Name KETOPROFEN
Phase Approved
Structure Type MOL
InChI Key DKYWVDODHFEZIM-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

(rs)-ketoprofen 19583RP Actron Actron ketoprofen Alrheumat Aneol Axorid Capisten Fenoket 200 Hydratropic acid, m-benzoyl- IDEA-033 Iso-k +18 more
10
Targets
38
Activities
2
Assay Types
30
PK Parameters
20
Publications
30
Known Names
20
Indications
1
Mechanisms

Molecular Properties

254.3
MW (Da)
3.11
ALogP
2
HBA
1
HBD
54.4
PSA (Ų)
0.85
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1986
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -profen
USAN Year 1972

Extended Properties

Molecular Formula C16H14O3
MW 254.29
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness -0.08

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cyclooxygenase inhibitor INHIBITOR Cyclooxygenase ✓ ✓

Indications

Acute Pain Arthralgia Arthritis, Rheumatoid Dysmenorrhea Myalgia Osteoarthritis Rheumatic Diseases Bursitis Inflammation Low Back Pain Migraine Disorders Osteoarthritis, Knee Postoperative Nausea and Vomiting Sprains and Strains Tendinopathy Wounds and Injuries Multiple Sclerosis Paget Disease, Extramammary Periodontitis Kidney Calculi

ATC Classification

M01AE03
ketoprofen
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M01AE53
ketoprofen, combinations
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M02AA10
ketoprofen
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN

Drug Warnings

Black Box Warning
cardiotoxicity
Country: United States
Black Box Warning
gastrointestinal toxicity
Country: United States
Black Box Warning
neurotoxicity
Country: United States

Activity Summary

IC50 31 meas. best 8.7
Ki 7 meas. best 5.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 8.7 7.9325 2.0 4
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 7.58 6.6929 26.0 7
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 7.46 6.9225 35.0 4
Prostaglandin G/H synthase 2
CHEMBL4102
 IC50 6.75 6.75 180.0 1
Rattus norvegicus
CHEMBL376
 IC50 6.7 6.7 200.0 1
Solute carrier family 22 member 6
CHEMBL1777665
 IC50 6.3 6.3 500.0 1
Solute carrier family 22 member 6
CHEMBL1641347
 IC50 5.89 5.87 1300.0 2
Solute carrier family 22 member 7
CHEMBL2073671
 Ki 5.74 5.74 1840.0 1
Unchecked
CHEMBL612545
 IC50 5.42 4.9614 3795.9 7
RAW264.7
CHEMBL612557
 IC50 5.15 5.15 7070.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 2.22 mL.min-1.kg-1 Homo sapiens
CL 1.6 mL.min-1.kg-1 Homo sapiens
CL 1.1 mL.min-1.kg-1 Homo sapiens
CL 1.6 mL.min-1.kg-1 Homo sapiens
CL 1.6 mL.min-1.kg-1 Homo sapiens
CL 53.7 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 3.0 uL.min-1.(10^6cells)-1 Homo sapiens
CL 74.9 mL.min-1.kg-1 Homo sapiens
CL 6.28 uL.min-1.(10^6cells)-1 Homo sapiens
CL 1.2 mL.min-1.kg-1 Homo sapiens
CL 1.74 mL.min-1.kg-1 Homo sapiens
CL 1.6 mL.min-1.kg-1 Homo sapiens
CL 3.3 mL.min-1.kg-1 Mus musculus
CL 6.0 uL.min-1.(10^6cells)-1 Homo sapiens
CL 1.6 mL.min-1.kg-1 Homo sapiens
F 80.0 % Homo sapiens
F 100.0 % Homo sapiens
Fu 0.008 - Homo sapiens
Fu 0.008 - Homo sapiens
Fu 0.095 - Mus musculus
Fu 0.024 - Canis lupus familiaris
Fu 0.014 - Macaca mulatta
Fu 0.011 - Rattus norvegicus
Fu 0.004 - Homo sapiens
Fu 0.017 - Not specified
Fu 0.988 - Homo sapiens
Fu 0.008 - Homo sapiens
Fu 0.008 - Homo sapiens
MRT 1.4 hr Homo sapiens
T1/2 20.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin G/H synthase 1 IC50 = 2.0 nM 8.7 Inhibition of COX-1 in human platelet in presence of arachidonic acid by human w... 37148849
Prostaglandin G/H synthase 1 IC50 = 2.0 nM 8.7 In vitro inhibition of cyclooxygenase-1 via inhibition of TXB2 generation in the... 11844666
Prostaglandin G/H synthase 1 IC50 = 14.0 nM 7.85 DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) -
Prostaglandin G/H synthase 2 IC50 = 26.0 nM 7.58 In vitro inhibition of PGE-2 generation by LPS-stimulated monocytes isolated fro... 11844666
Prostaglandin G/H synthase 2 IC50 = 26.0 nM 7.58 Inhibition of COX-2 in LPS-stimulated human monocytes by human whole blood assay 37148849
Prostaglandin G/H synthase 1 IC50 = 35.0 nM 7.46 Inhibition of ovine COX-1 by EIA method 38626522
Prostaglandin G/H synthase 2 IC50 = 61.0 nM 7.21 Inhibition of recombinant human COX-2 preincubated for 15 mins by fluorescence a... 26487917
Prostaglandin G/H synthase 1 IC50 = 67.0 nM 7.17 Inhibition of Ovine COX-1 preincubated for 15 mins by fluorescence analysis 26487917
Prostaglandin G/H synthase 1 IC50 = 110.0 nM 6.96 Inhibition of ovine COX1 assessed as reduction in PGH2 production by enzyme immu... 29980364
Prostaglandin G/H synthase 2 IC50 = 164.0 nM 6.79 Inhibition of human recombinant COX-2 by EIA method 38626522
Prostaglandin G/H synthase 2 IC50 = 180.0 nM 6.75 Inhibition of ovine COX2 assessed as reduction in PGH2 production by enzyme immu... 29980364
Rattus norvegicus IC50 = 200.0 nM 6.7 Percent inhibition of edema was measured by adjuvant arthritis paw edema (rat) a... 6502598
Prostaglandin G/H synthase 1 IC50 = 330.0 nM 6.48 Inhibition of COX1 in human whole blood 18667313
Solute carrier family 22 member 6 IC50 = 500.0 nM 6.3 TP_TRANSPORTER: inhibition of MTX uptake in Xenopus laevis oocytes 11099697
Prostaglandin G/H synthase 2 IC50 = 690.0 nM 6.16 Inhibition of COX2 in human whole blood 18667313
Prostaglandin G/H synthase 2 IC50 = 785.0 nM 6.11 DRUGMATRIX: Cyclooxygenase COX-2 enzyme inhibition (substrate: Arachidonic acid) -
Prostaglandin G/H synthase 1 IC50 = 800.0 nM 6.1 Inhibition of purified ovine COX1 pre-treated for 1 hr before 10-acetyl-3,7-dihy... 25221653
Solute carrier family 22 member 6 IC50 = 1300.0 nM 5.89 TP_TRANSPORTER: inhibition of Adefovir uptake in OAT1-expressing CHO cells 10991954
Solute carrier family 22 member 6 IC50 = 1400.0 nM 5.85 TP_TRANSPORTER: inhibition of 6-Carboxyfluorescein uptake in OAT1-expressing CHO... 10929807
Solute carrier family 22 member 7 Ki = 1840.0 nM 5.74 TP_TRANSPORTER: inhibition of Salicylate uptake in Oat2-expressing LLC PK1 cells -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 323
- 10.1039/C5MD00551E No relevant target 28
16472241 10.2174/1570163043334794 Hepatotoxicity 18
6502598 10.1021/jm00378a027 Rattus norvegicus 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
16789751 10.1021/jm060230+ ADMET 9
26360048 10.1016/j.ejmech.2015.08.014 Mus musculus 9
20926620 10.1124/dmd.110.035600 HEK293 9
24996140 10.1016/j.ejmech.2014.06.032 Mus musculus 9
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
940112 10.1021/jm00229a017 Rattus norvegicus 8
17418579 10.1016/j.bmc.2007.03.040 ADMET 8
38286094 10.1016/j.ejmech.2024.116176 Rattus norvegicus 7
27561714 10.1016/j.bmcl.2016.08.021 NON-PROTEIN TARGET 6
21282406 10.1124/dmd.110.037457 Nucleic Acid 5
28259627 10.1016/j.bmcl.2017.02.036 Mus musculus 5
38286094 10.1016/j.ejmech.2024.116176 ADMET 5
21282406 10.1124/dmd.110.037457 Plasma 5

Data from ChEMBL 36 via Core Engine